I've always been curious about Bill James as to his interest in gaming. It would seem logical that such a baseball historian and metrics man would take an interest in stat-based baseball game simulations. James was 12 years old when S-O-M was created.

I did a Wiki search on "Out Of The Park" (OOTP) Baseball, a sim game that was first released in 1999. Bill James is mentioned as being one prominent person who has played this game. I don't know that James has ever had an interest in Strat-O-Matic or many of the other baseball sim games out there. It makes sense that James, who was hired as an executive with the Red Sox not long after the release of OOTP Baseball, would gravitate to that particular sim game because it incorporates many aspects of the game that go beyond what sim games like Strat or ABPA do. Things that are pertinent to what James, owner John Henry, GM at-the-time Theo Epstein--now Dave Dombrowski--, etc. would be involved in, whereas in Strat we are strictly the manager, though one could easily home brew other aspects into the S-O-M game.